I'm a 40 year old freelancer in the film business. My gross annual income averages $150,000 (though since I'm self-employed, work can be sometimes volatile and inconsistent). My wife and I own a house (purchased for $800,000, 5 years ago. Now estimated worth over $1.3M). We have $590,000 left on the mortgage = 30yr fixed at 4.0%

I have $220,000 in cash savings and $34,000 in 401k. My wife has $19,000 in her 401k. She works for me (i.e. also self-employed).

Currently my cash is in an online savings account(!!), and is gaining a terrible 0.6% interest or thereabouts. Obviously I need to invest it more aggressively.

I was advised by my accountant that if I'm going to invest on the stock market, that I should consider paying off a chunk (say $50k) of our mortgage at the same time (as a way of 'diversifying' our investing by reducing our mortgage burden).

If I were to do that, and also keep about $50,000 in savings (rainy day), that leaves me with $120,000 to invest in the stock market.

I'm considering Robo-investors (Wealthfront, Betterment etc) vs a human financial manager. Can you advise on the pros/cons of robo-investors vs humans, and also the mortgage payoff etc. Thanks!

Maybe you want to do both, some with a robo and some with a "live" person until you can get a feel for which you prefer. If you do either or both interview at least three financial advisors. If they don't feel right, trust your gut, than move on. Robo is still new to the financial world so be more careful with that.

With both you and your wife totally dependent on one source of income, self-employment within the same business, you have a potentially precarious situation. Not sure your accountant is correct with the $50k. If something happens and you need the money how are you going to get it back out of your house quickly. Think about what happened in 2008 and several years beyond. Can it happen again? Nobody thought it could happen the first time. You need easy access to your money until you can build your business more and have a larger pot of money to fall back on.

The final decision is yours. I hope this might get you to think long and hard about this before you make a decision. You did say work can be volatile and inconsistent which affects both of you.

I'm finally setup with my Vanguard account and have decided to do the following:

1. Paying an additional $700 towards the mortgage each month, which means we're set to pay it off by 2036 (in 20 ys-when I'm aged 60). I decided not to pay-off more for now since that liquidity is important due to my volatile earning (i.e. the possible need for more cash, which if I pay off house would just be invested in the house).

2. Invest $50,000 with Vanguard (probably using their advisor service...for a year at least so I can learn).

3. Invest $50,000 with a Robo-advisor (probably Wealthfront)..for a year at least. After that year or more I'll see which is performing better. Since I have exactly the same amount invested they should be pretty easy to compare. Also, after that year (or more) I may opt to not do the 'Advisor' services at Vanguard and just self-invest in various Index Funds / ETFS (or just the Vanguard S&P like you suggested).

4. Keep $50,000+ in Emergency Fund. While it might be foolish to keep this much in a Savings account, since i'm a freelancer and my income is highly volatile, I do need the liquidity on occasion (so as not to have to dip into the investment accounts). That said, can anyone recommend a more lucrative way of keeping 'SAFE' money. E,g, half in savings, and half say in Treasury bonds? (with a 1-yr maturity or something). That way the whole $50k is not going to waste...

5. $70,000 is now in my 401k. Due to tax deadline issues I had to rollover my single- 401k to a new Financial Advisor. He happens to be with Merrill Lynch (and I believe is charging 1.1--1.3% in fees/commissions. I thought about moving this soon to a 401k at Vanguard, but I discovered that Vanguard cannot offer account management / rebalancing services for 401k's (which ML does), so I'm undecided about what to do with this money.

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I'm finally setup with my Vanguard account and have decided to do the following:

1. Paying an additional $700 towards the mortgage each month, which means we're set to pay it off by 2036 (in 20 ys-when I'm aged 60). I decided not to pay-off more for now since that liquidity is important due to my volatile earning (i.e. the possible need for more cash, which if I pay off house would just be invested in the house).

2. Invest $50,000 with Vanguard (probably using their advisor service...for a year at least so I can learn).

3. Invest $50,000 with a Robo-advisor (probably Wealthfront)..for a year at least. After that year or more I'll see which is performing better. Since I have exactly the same amount invested they should be pretty easy to compare. Also, after that year (or more) I may opt to not do the 'Advisor' services at Vanguard and just self-invest in various Index Funds / ETFS (or just the Vanguard S&P like you suggested).

4. Keep $50,000+ in Emergency Fund. While it might be foolish to keep this much in a Savings account, since i'm a freelancer and my income is highly volatile, I do need the liquidity on occasion (so as not to have to dip into the investment accounts). That said, can anyone recommend a more lucrative way of keeping 'SAFE' money. E,g, half in savings, and half say in Treasury bonds? (with a 1-yr maturity or something). That way the whole $50k is not going to waste...

5. $70,000 is now in my 401k. Due to tax deadline issues I had to rollover my single- 401k to a new Financial Advisor. He happens to be with Merrill Lynch (and I believe is charging 1.1--1.3% in fees/commissions. I thought about moving this soon to a 401k at Vanguard, but I discovered that Vanguard cannot offer account management / rebalancing services for 401k's (which ML does), so I'm undecided about what to do with this money.

Any advice on any of the above points would be most appreciated!

The choices you have made strike me as very sensible ones. You're obviously well aware that it's important to diversify and not risk everything in a single investment.

If you're planning on managing your investments more actively, then a couple of recommendations would be Mebane Faber's 'The Ivy Portfolio', and Michael Covel's 'Trend Following'.

Finally, Vanguard is a good choice of broker, and you can get commission free trading on a lot of the Vanguard ETFs. These costs can really stack up over the term, so they're best kept to a minimum.

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One of the primary benefits of investing in the stock market is the chance to grow your money. Over time, the stock market tends to rise in value, though the prices of individual stocks rise and fall daily. Investments in stable companies that are able to grow tend to make profits for investors.

One of the primary benefits of investing in the stock market is the chance to grow your money. Over time, the stock market tends to rise in value, though the prices of individual stocks rise and fall daily. Investments in stable companies that are able to grow tend to make profits for investors.

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